CN104272488A - Organic light emitting diode - Google Patents
Organic light emitting diode Download PDFInfo
- Publication number
- CN104272488A CN104272488A CN201380024222.0A CN201380024222A CN104272488A CN 104272488 A CN104272488 A CN 104272488A CN 201380024222 A CN201380024222 A CN 201380024222A CN 104272488 A CN104272488 A CN 104272488A
- Authority
- CN
- China
- Prior art keywords
- layer
- electron transport
- emitting device
- organic light
- light emitting
- Prior art date
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- Granted
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- 229910052751 metal Inorganic materials 0.000 claims abstract description 45
- 239000002184 metal Substances 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000002019 doping agent Substances 0.000 claims abstract description 27
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 18
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims description 80
- 239000000126 substance Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000011368 organic material Substances 0.000 claims description 33
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 15
- 238000000149 argon plasma sintering Methods 0.000 claims description 14
- 125000002524 organometallic group Chemical group 0.000 claims description 13
- -1 rare earth metal ion Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 claims description 4
- 125000003375 sulfoxide group Chemical group 0.000 claims description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
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- 229910052693 Europium Inorganic materials 0.000 claims description 3
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- 229910052689 Holmium Inorganic materials 0.000 claims description 3
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- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000524 functional group Chemical group 0.000 claims description 3
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- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical class C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 claims description 2
- FZTBAQBBLSYHJZ-UHFFFAOYSA-N 2-phenyl-1,3-oxazol-4-ol Chemical class OC1=COC(C=2C=CC=CC=2)=N1 FZTBAQBBLSYHJZ-UHFFFAOYSA-N 0.000 claims description 2
- CCMLIFHRMDXEBM-UHFFFAOYSA-N 2-phenyl-1,3-thiazol-4-ol Chemical class OC1=CSC(C=2C=CC=CC=2)=N1 CCMLIFHRMDXEBM-UHFFFAOYSA-N 0.000 claims description 2
- HJJXCBIOYBUVBH-UHFFFAOYSA-N 2-phenyl-1h-benzimidazol-4-ol Chemical class N1C=2C(O)=CC=CC=2N=C1C1=CC=CC=C1 HJJXCBIOYBUVBH-UHFFFAOYSA-N 0.000 claims description 2
- VHRHRMPFHJXSNR-UHFFFAOYSA-N 2-phenylpyridin-3-ol Chemical class OC1=CC=CN=C1C1=CC=CC=C1 VHRHRMPFHJXSNR-UHFFFAOYSA-N 0.000 claims description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical class OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 claims description 2
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- JUTIJVADGQDBGY-UHFFFAOYSA-N anthracene photodimer Chemical group C12=CC=CC=C2C2C(C3=CC=CC=C33)C4=CC=CC=C4C3C1C1=CC=CC=C12 JUTIJVADGQDBGY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000732 arylene group Chemical group 0.000 claims description 2
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- SISAYUDTHCIGLM-UHFFFAOYSA-N bromine dioxide Inorganic materials O=Br=O SISAYUDTHCIGLM-UHFFFAOYSA-N 0.000 claims description 2
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- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 2
- 125000005266 diarylamine group Chemical group 0.000 claims description 2
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052730 francium Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
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- 229910001635 magnesium fluoride Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000000619 oxo-lambda(3)-bromanyloxy group Chemical group *OBr=O 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- KELCFVWDYYCEOQ-UHFFFAOYSA-N phenanthridin-1-ol Chemical compound C1=CC=CC2=C3C(O)=CC=CC3=NC=C21 KELCFVWDYYCEOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YSZJKUDBYALHQE-UHFFFAOYSA-N rhenium trioxide Chemical compound O=[Re](=O)=O YSZJKUDBYALHQE-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
- H10K50/131—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit with spacer layers between the electroluminescent layers
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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
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Abstract
The present specification relates to an organic light emitting diode, comprising: a first electrode; a second electrode; and two or more light emitting units provided between the first electrode and the second electrode, wherein a charge generating layer is formed between two adjacent light emitting units among the light emitting units, an electron transport layer is provided between the light emitting unit close to the first electrode of the two adjacent light emitting units and the charge generating layer. The electron transport layer comprises: a first electron transport layer doped with an n-type dopant; and a second electron transport layer doped with metal salt, a metal oxide or organic metal salt.
Description
Technical Field
The present invention relates to an organic light emitting device. More particularly, the present invention relates to an organic light emitting device including two or more light emitting units.
This application claims and has priority to korean patent application No. 10-2012-0058232 filed by the korean intellectual property office on 31/5/2012, the entire contents of which are incorporated herein by reference.
Background
Organic Light Emitting Devices (OLEDs) are typically formed from two electrodes (an anode and a cathode) with one or more layers of organic material disposed between the electrodes. In the organic light emitting device having such a structure, when a voltage is applied between two electrodes, holes from an anode and electrons from a cathode flow into the organic material layer. The holes and electrons combine to form excitons (exiton). The excitons drop to the ground state and emit photons corresponding to the energy difference. According to this principle, the organic light emitting device generates visible light. An information display device or an illumination apparatus can be manufactured by using the organic light emitting device.
In order to expand the application range of the organic light emitting device and commercialize the organic light emitting device, techniques for increasing the efficiency of the organic light emitting device and reducing the driving voltage have been continuously developed.
Disclosure of Invention
Technical problem
An organic light emitting device is described that includes more than two light emitting cells.
Technical scheme
According to one embodiment of the present invention, an organic light emitting device includes a first electrode, a second electrode, and two or more light emitting units provided between the first electrode and the second electrode. Herein, between the light emitting units, a charge generation layer is provided between two light emitting units adjacent to each other, an electron transport layer is provided between the charge generation layer and the light emitting units, the light emitting units are adjacent to first electrodes of the two adjacent light emitting units, and the electron transport layer includes a first electron transport layer doped with an n-type dopant, and a second electron transport layer doped with a metal salt, a metal oxide, or an organic metal salt.
According to another embodiment of the present invention, in the organic light emitting device, an additional electron transport layer is provided between the second electrode and the light emitting unit adjacent to the second electrode, and the additional electron transport layer includes a first electron transport layer doped with an n-type dopant, and a second electron transport layer doped with a metal salt, a metal oxide, or an organic metal salt.
According to still another embodiment of the present invention, in the organic light emitting device, an additional electron transport layer is provided between the second electrode and the light emitting unit adjacent to the second electrode, and the additional electron transport layer includes a first electron transport layer doped with an n-type dopant, and a second electron transport layer doped with a metal salt, a metal oxide, or an organic metal salt. Further, a further charge generation layer is provided between the second electrode and the further electron transport layer.
Advantageous effects
Embodiments according to the present invention can provide an organic light emitting device having a significantly reduced driving voltage, excellent light emitting efficiency, and a long life span, and having improved light emitting efficiency compared to a conventional organic light emitting device.
Drawings
Fig.1 illustrates a layer structure of an organic light emitting device according to an embodiment of the present invention.
Fig.2 illustrates the structure of a charge generation layer included in an organic inventive device according to an embodiment of the present invention.
Fig.3 is a schematic view of the charge flow in the device of fig. 1.
Fig.4 illustrates a layer structure of a general organic light emitting device.
Fig.5 is a schematic view of the charge flow in the device of fig. 4.
Fig.6 is a view illustrating a layer structure of an organic light emitting device according to another embodiment of the present invention.
Fig.7 illustrates a layer structure of an organic light emitting device according to still another embodiment of the present invention.
Fig.8 illustrates a layer structure of an organic light emitting device according to still another embodiment of the present invention.
Fig.9 illustrates a layer structure of an organic light emitting device according to still another embodiment of the present invention.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. In the following description, reference is made to specific reference numerals in the drawings, however, embodiments of the present invention are not limited to the corresponding reference numerals in the drawings, and the related description is entirely applied to the corresponding configurations.
In the present invention, n-type means n-type semiconductor properties. In other words, n-type refers to a property of accepting electrons by injection or transporting electrons through a lowest occupied molecular orbital (LUMO) level, and may be defined as a material property in which electron mobility is greater than hole mobility. In contrast, p-type refers to p-type semiconductor properties. In other words, p-type refers to a property of receiving holes by injection or transporting holes through a Highest Occupied Molecular Orbital (HOMO) level, and may be defined as a material property in which hole mobility is greater than electron mobility. In the present invention, the compound or organic material layer having n-type properties means an n-type compound or an n-type organic material layer. Further, the compound or the organic material layer having a p-type property means a p-type compound or a p-type organic material layer. Further, n-type doping refers to doping to have n-type properties.
Fig.1 is a schematic view of a layer structure of an organic light emitting device according to an embodiment of the present invention, and fig.3 illustrates a flow of charges in the organic light emitting device shown in fig. 1.
As shown in fig.1, in an organic light emitting device according to an embodiment of the present invention, two light emitting units (210, 220) are disposed between a first electrode (110) and a second electrode (120), and a charge generation layer (510) and an electron transport layer forming two layers are disposed between the two light emitting units (210, 220). At this time, the charge generation layer (510) is disposed adjacent to the light emitting cell (220) adjacent to the second electrode (120), and the electron transport layer is disposed adjacent to the light emitting cell (210) adjacent to the first electrode (110). The electron transport layer includes: a first electron transport layer (310) doped with an n-type dopant, and a second electron transport layer (410) doped with a metal salt, a metal oxide, or an organic metal salt, the first electron transport layer (310) being disposed adjacent to the charge generation layer (510), and the second electron transport layer (410) being disposed adjacent to the light emitting unit (210) adjacent to the first electrode (110).
According to fig.1, two light emitting cells (210, 220) are provided between a first electrode (110) and a second electrode (120). A charge generation layer (510) is provided between the two light emitting cells (210, 220). The first electron transport layer (310) and the second electron transport layer (410) are provided between the charge generation layer (510) and the light emitting cell (210), the light emitting cell (210) being disposed adjacent to a first electrode in the light emitting cell. Fig.1 shows the following structure: the light emitting unit (210), the second electron transport layer (410), the first electron transport layer (310), the charge generation layer (510), the light emitting unit (220), and the second electrode (120) are stacked on the first electrode (110), however, fig.1 also includes the following structure instead: a light emitting unit (220), a charge generation layer (510), a first electron transport layer (310), a second electron transport layer (410), a light emitting unit (210), and a first electrode (110) are stacked on a second electrode (120).
In the present invention, the adjacent means that the positional relationship of the closest layer among the mentioned layers is the adjacent. For example, adjacent to two light emitting units refers to a positional relationship closest to the two light emitting units among the plurality of light emitting units. Adjacent as described above may refer to the case of two layers that are physically connected or other undescribed layers that may be interposed between the two layers. For example, the light emitting cell adjacent to the second electrode refers to a light emitting cell positioned closest to the second electrode among the light emitting cells. In addition, the second electrode and the light emitting cell may be physically connected, however, other layers than the light emitting cell may be disposed between the second electrode and the light emitting cell. However, the charge generation layer is provided between two adjacent light emitting cells.
In the present invention, the first electrode and the second electrode are used for applying an external voltage, and are not particularly limited as long as they have conductivity. For example, the first electrode may be an anode and the second electrode may be a cathode.
In the present invention, the light emitting unit (210, 220) is not particularly limited as long as it is a unit having a light emitting function. For example, the light emitting unit (210, 220) may include more than one light emitting layer. When necessary, the light emitting unit (210, 220) may include more than one organic material layer in addition to the light emitting layer.
In one embodiment, the light-emitting layer may comprise a material that is separated by a combinationThe transported holes and electrons are able to emit light in the visible region. As the light-emitting layer material, a material known in the art can be used. For example, a material having a good quantum effect (quantum efficiency) of fluorescence and phosphorescence may be used. Specific examples of the light emitting layer material include 8-hydroxy-quinoline aluminum complex (Alq)3) Carbazoles, dimeric styryl compounds, BAlq, 10-hydroxybenzoquinoline metal compounds, benzoxazole, benzothiazole and benzimidazole compounds, poly (p-phenylethene) (PPV) -based polymers, spiro compounds, polyfluorenes, rubrene, and the like, but are not limited thereto.
In one embodiment, the light emitting unit (210, 220) may be additionally provided and include more than one organic material layer in addition to the light emitting layer. In addition, the organic material may include a hole transport layer, a hole injection layer, a layer for transporting and injecting holes, a buffer layer, an electron blocking layer, an electron transport layer, an electron injection layer, a layer for transporting or injecting electrons, a hole blocking layer, and the like. Here, the hole transport layer, the hole injection layer, the layer for transporting or injecting holes, or the electron blocking layer may be disposed closer to the first electrode (110) than the light emitting layer. An electron transport layer, an electron injection layer, a layer for transporting and injecting electrons, or a hole blocking layer may be disposed closer to the second electrode (120) than the light emitting layer. The use of the hole blocking layer may be determined according to the properties of the light emitting layer. For example, when the property of the light emitting layer approaches an n-type property, the hole blocking layer may not be used, however, when the property of the light emitting layer approaches a p-type property, the use of the hole blocking layer may be considered. Further, the use of the hole blocking layer may also be determined in consideration of the relationship between the HOMO level of the light emitting layer and the HOMO level of the electron transport layer. When the HOMO energy level of the light emitting layer has a value greater than that of the electron transport layer, it may be considered to add a hole blocking layer. In this case, however, when the HOMO level of the electron transport layer is larger than that of the light emitting layer, the electron transport layer itself may serve as a hole blocking layer. As an example, by using two or more electron transport layer materials, the electron transport layer can function as both the electron transport layer and the hole blocking layer.
In the present invention, the charge generation layer (510) is a layer that generates charges without applying an external voltage, and the charge generation layer can cause two or more light emitting cells included in the organic light emitting device to emit light by generating charges between the light emitting cells (210, 220). The charge generation layer 510 according to one embodiment of the present invention may include an n-type organic material layer and a p-type organic material layer. At this time, the n-type organic material layer (hereinafter, referred to as "n-type charge generation layer") of the charge generation layer (510) is disposed closer to the first electrode (110) than the p-type organic material layer (hereinafter, referred to as "p-type charge generation layer") of the charge generation layer (510). Fig.2 shows an embodiment of the charge generation layer. Fig.2 shows a charge generation layer including an n-type charge generation layer (512) disposed adjacent to a first electrode (110) and a p-type charge generation layer (511) disposed adjacent to a second electrode.
In one embodiment, the LUMO energy level of the n-type charge generation layer (512) is equal to or greater than the HOMO energy level of the p-type charge generation layer (511), which makes charge generation more efficient. For example, the LUMO level of the n-type charge generation layer (512) may be 5 to 7eV, and the HOMO level of the p-type charge generation layer may be 5eV or more.
In the present invention, the energy level refers to the magnitude of energy. Therefore, when the energy level is shown as being in the (-) direction from the vacuum level, this means that the energy level is the absolute value of the corresponding energy value. For example, the HOMO level refers to the distance from the vacuum level to the highest occupied molecular orbital. Further, the LUMO energy level refers to the distance from the vacuum level to the lowest occupied molecular orbital.
The charge may be generated by forming an NP connection between the n-type charge generation layer (512) and the p-type charge generation layer (511). At this time, the LUMO level of the n-type charge generation layer (512) and the HOMO level of the p-type charge generation layer (511) may be adjusted in consideration of the energy level relationship between adjacent organic material layers. For example, in the n-type charge generation layer (512) and the p-type charge generation layer (511), the difference between the HOMO level of the p-type charge generation layer (511) and the LUMO level of the n-type charge generation layer (512) can be adjusted to 2eV or less or 1eV or less. The energy level difference may be greater than or equal to-1 eV and less than or equal to 1eV, and greater than or equal to 0.01eV and less than or equal to 1eV, as judged from the energy levels of commercially available materials.
Holes generated between the n-type charge generation layer 512 and the p-type charge generation layer 511 are quickly injected into the HOMO level of the p-type charge generation layer 511. When the LUMO level of the n-type charge generation layer (512) is greater than the HOMO level of the p-type charge generation layer (511), an increase in driving voltage can be avoided because an NP connection is rapidly formed. In the present invention, NP connection can be formed not only when the n-type organic material layer 512 and the p-type organic material layer 511 are physically connected but also when the above energy relationship is satisfied.
When the NP junction is formed, holes or electrons are rapidly formed by an applied voltage or light source. That is, holes or electrons are simultaneously generated between the n-type charge generation layer (512) and the p-type charge generation layer (511) through NP connection. Electrons are transported to the first electron transport layer (310) and the second electron transport layer (410) via the n-type charge generation layer (512). Holes are transported to the p-type charge generation layer (511). That is, when the LUMO level of the n-type charge generation layer (512) is greater than the HOMO level of the p-type charge generation layer (511), holes and electrons are rapidly generated, and an increase in driving voltage for hole injection can be avoided.
In one embodiment of the present invention, the HOMO level of the p-type charge generation layer (511) may be 5eV or more. When it is 5eV or more, holes can be efficiently injected into the adjacent light emitting cell.
As a material for the p-type charge generation layer (511), an arylamine-based compound can be used. One example of the aromatic amine-based compound includes a compound of the following chemical formula 1.
[ chemical formula 1]
In the above chemical formula 1, Ar1、Ar2And Ar3Each independently hydrogen or a hydrocarbyl group. Wherein Ar is1、Ar2And Ar3At least one of which may comprise an aromatic hydrocarbon substituent, and each substituent may be the same or they may be composed of different substituents. When Ar is1、Ar2And Ar3When not aromatic, it may be hydrogen; a linear, branched or cyclic aliphatic hydrocarbon; or a heterocyclic group containing N, O, S or Se.
Specific examples of the above chemical formula 1 include the following chemical formula, however, the scope of the embodiments described in the present invention is not limited thereto.
In one embodiment, the n-type charge generation layer 512 may be composed of only organic materials. In another embodiment, the n-type charge generation layer (512) may further comprise a transition metal oxide, e.g., MoO3、V2O7And ReO3. In yet another embodiment, the n-type charge generation layer (512) may include an n-type dopant. At this time, the n-type dopant may be an organic material or an inorganic material. When the n-type dopant is an inorganic material, it may contain an alkali metal such as Li, Na, K, Rb, Cs, or Fr; alkaline earth metals, such as Be, Mg, Ca, Sr, Ba or Ra; rare earth metals such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y or Mn; or comprisesA metal compound of one or more of the above metals. In addition, the n-type dopant may also be a material containing cyclopentadiene, cycloheptatriene, 6-membered heterocyclic rings or condensed rings containing these rings. In this case, the doping concentration may be in the range of 0.01 to 50 wt% or 1 to 10 wt%. In the above doping concentration, the efficiency can be prevented from being lowered by absorption of light.
The n-type charge generation layer (512) according to one embodiment may include a compound of the following chemical formula 2.
[ chemical formula 2]
In the above chemical formula 2, A1To A6Each is hydrogen, halogen atom, cyano (-CN), nitro (-NO)2) Sulfonyl (-SO)2R), sulfoxide group (-SOR), sulfonamide group (-SO)2NR), sulfate (-SO)3R), trifluoromethyl (-CF)3) An ester group (-COOR), an amide group (-CONHR or-CONRR'), a substituted or unsubstituted straight or branched C1-C12Alkoxy, substituted or unsubstituted straight or branched C1-C12Alkyl, substituted or unsubstituted straight or branched C2-C12Alkenyl groups, substituted or unsubstituted aromatic or non-aromatic heterocycles, substituted or unsubstituted aryl groups, substituted or unsubstituted mono or diarylamines, substituted or unsubstituted aralkylamines, and the like. Herein, R and R' are each a substituted or unsubstituted C1-C60Alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted 5 to 7 membered heterocyclic ring, and the like.
Examples of the compound of the above chemical formula 2 include compounds of the following chemical formulae 2-1 to 2-6.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
[ chemical formulas 2-4]
[ chemical formulas 2 to 5]
[ chemical formulas 2 to 6]
In one embodiment, the n-type charge generation layer (512) may be formed of only one layer or may include more than two layers. When there are more than two layers, the layers may be formed of the same material or may be formed of different materials.
As an example, when two or more layers are formed of the same material, one layer may be undoped and the remaining layers may be n-type doped. For example, the n-type charge generation layer (512) may have the following structure: a layer formed of the compound of chemical formula 2 is stacked with a layer of the compound of chemical formula 2 doped with an n-type dopant.
As another exampleFor example, the n-type charge generation layer 512 may be a layer structure of an inorganic material layer and an organic material layer. Specifically, the n-type charge generation layer may be made of MoO3A layer formed with the layer of the compound of chemical formula 2.
When the n-type charge generation layer is formed of two or more layers, the layers may be stacked according to the LUMO energy level value. Specifically, when the first layer is formed of a material having a high LUMO level, electron transport can be made smooth because the energy barrier between the two materials can be reduced. Therefore, an increase in the driving voltage can be avoided. For example, because of MoO3Has a LUMO level of about 6.7eV and the LUMO level of the compound of the above chemical formula 2-1 is 5.7eV, MoO may be formed first3And (3) a layer.
In the present invention, the electron transport layer may include a first electron transport layer (310) and a second electron transport layer (410). The first electron transport layer (310) is doped with an n-type dopant. The first electron transport layer (310) functions to make the charge generation layer (510) effectively satisfy the Fermi level (Fermi level) by doping with an n-type dopant. Thus, the first electron transport layer (310) may improve electron injection properties by reducing the energy barrier for electron injection of the charge generation layer (510). The LUMO energy level of the n-type doped first electron transport layer has a fermi energy level (E) closer to the LUMO energy level of the undoped electron transport layerf) The characteristic of (c). Thus, the energy barrier between the two layers is reduced, and thus, the electron injection properties can be improved (refer to j. mater. chem.,2011,21, 17476-.
The difference between the LUMO level of the first electron transport layer (310) and the LUMO level of the n-type charge generation layer (512) adjacent thereto may be 5eV or less.
In one embodiment, as the n-type dopant included in the first electron transport layer (310), an alkali metal, such as: such as Li, Na, K, Rb, Cs or Fr; alkaline earth metals, such as Be, Mg, Ca, Sr, Ba or Ra; rare earth metals such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y or Mn; or a metal compound comprising one or more of the foregoing metals. Herein, the content of the n-type dopant may be 1 to 50% by weight based on the total weight of the first electron transport layer material (310). In the present invention, a method known in the art may be used as a method of doping an n-type dopant, and the scope of the present invention is not limited to any particular method.
The first electron transport layer (310) may have a thickness in the range of 50 to 100 angstroms. When the thickness of the first electron transport layer (310) including the n-type dopant is 100 angstroms or less, a reduction in light emission effect due to absorption of visible light may be prevented.
According to an embodiment of the present invention, the organic light emitting device further comprises a second electron transport layer (410) doped with one or more types selected from metal salts, metal oxides, and organometallic salts. As the metal salt, an alkali metal halide or an alkaline earth metal halide, for example, LiF, NaF, KF, RbF, CsF, MgF2、CaF2、SrF2、BaF2、LiCl、NaCl、KCl、RbCl、CsCl、MgCl2、CaCl2、SrCl2Or BaCl2. As metal oxides, use may be made of alkali metal oxides or alkaline earth metal oxides, for example LiO2、NaO2、BrO2、Cs2O, MgO or CaO. As the organometallic, Liq, Naq, Kq, and the like of the following chemical formula 3 can be used.
[ chemical formula 3]
The second electron transport layer (410) may have a thickness ranging from 50 to 500 angstroms, more specifically, from 50 to 200 angstroms. When the thickness is in the above range, an increase in driving voltage can be effectively prevented.
The metal salt, metal oxide, or organometallic salt may be present in an amount of 1 to 99 weight percent, specifically 10 to 50 weight percent, based on the total weight of the second electron transport layer material (410).
By doping a metal salt, a metal oxide, or an organic metal salt, the second electron transport layer (410) may facilitate smooth transport of electrons, which are transported to the light emitting unit (210) adjacent to the first electrode (110) via the charge generation layer (510) and the first electron transport layer (310). In addition, by preventing holes from being transferred from the light emitting unit (210) to the charge generation layer (510) through the first electron transport layer (310), the second electron transport layer (410) may significantly reduce a driving voltage and improve light emitting efficiency, and may additionally contribute to realization of a device having a long lifetime.
Hereinafter, referring to fig.3, a flow of charges between the first electron transport layer (310), the second electron transport layer (410), and the charge generation layer (510) in the organic light emitting device shown in fig.1 will be described. In fig.3, (-) denotes an electron and (+) denotes a hole. The dashed lines represent electron flow and the solid lines represent hole flow. The designation X means neither electron nor hole flow. As described above, charges are generated due to the separation of holes and electrons in the charge generation layer (510), and the electrons move to the first electron transport layer (310) and the second electron transport layer (410). Conversely, holes do not move from the second electron transport layer (410) to the charge generation layer (510).
When the first electron transport layer (310) and the second electron transport layer (410) shown in fig.1 are not present in the organic light emitting device, high light emitting efficiency as described above cannot be achieved. For example, as shown in fig.4, when the organic light emitting device includes one electron transport layer instead of two electron transport layers having different properties, flowing holes that do not participate in light emission may be generated in the light emitting unit.
For example, the following scenarios may be considered: the organic light emitting device includes two light emitting cells (21, 22) each between a first electrode (11) and a second electrode (12), and between the two light emitting cells (21, 22), an electron transport layer (31) (e.g., an n-type doped electron transport layer) is formed on a side of the light emitting cell (21) adjacent to the first electrode (11), and a charge generation layer (51) is formed on a side of the light emitting cell (22) adjacent to the second electrode (12). With regard to the flow of charges in this case, since holes are transferred from the electron transport layer (31) to the charge generation layer (51) as shown in fig.5, flowing holes that do not participate in light emission may be generated in the light emitting unit (21), and thus the efficiency of the device may be reduced.
The present inventors have found that even when an n-type doped electron transport layer doped with an n-type dopant (e.g., Ca) is used as the electron transport layer (31), the efficiency of the device is not high, the driving voltage is increased, and the lifetime of the device is reduced.
However, in the organic light emitting device in the embodiment described in the present invention, as shown in the diagram of fig.3, the second electron transport layer (410) doped with one or more types selected from metal salts, metal oxides, and organic metal salts plays a role of preventing holes transported from the light emitting unit (210) from being transferred to the charge generation layer (510) via the first electron transport layer (310) doped with an n-type dopant. Accordingly, electrons injected from the charge generation layer (510) may be efficiently raised to the LUMO level of the first electron transport layer (310) doped with an n-type dopant. Thus. The electrons can be rapidly transmitted to the light emitting unit (210).
Therefore, according to the embodiments of the present invention, the driving voltage may be significantly reduced, the efficiency of the device may be significantly improved, and the lifespan of the device may be increased. When holes are not properly confined in the light-emitting layer and transferred to the hole-generating layer, it is difficult for electrons to be injected from the hole-generating layer to the first electron-transporting layer; injecting a second electron transport layer from the first electron transport layer; and finally injected from the second electron transport layer to the light emitting layer. In this case, more energy is required to inject electrons into the light emitting layer, and thus an increase in driving voltage may be caused. When electrons are difficult to inject, charge imbalance will result, which may affect the lifetime of the device. In the described embodiments of the invention, by facilitating electron injection, the lifetime of the device can be increased, thereby minimizing charge imbalance. In the present invention, the second electron transport layer (410) functions to effectively block holes, and thus, contributes to improvement of electron injection capability of the adjacent first electron transport layer (310).
In the present invention, as the organic material doped to the first electron transport layer (310) and the second electron transport layer (410), that is, one kind of host material, an organic material that can function to transport electrons can be used. The same or different materials may be used as host materials for the first electron transport layer and the second electron transport layer.
As an example of a host material for the first and second electron transport layers (310, 410), an organic material or an organometallic compound may be used.
Specifically, as will be described in detail below, a hydrocarbon electron transport material, for example, an electron transport material having an n-type substituent in an anthracene core or an electron transport material having an n-type substituent in a dianthracene core, or an organometallic complex may be used. Herein, the n-type substituent means an electron-withdrawing group, and examples thereof include a cyclic compound containing a hetero atom (e.g., N, O and S) in the ring, and a cyclic compound in which a functional group (e.g., -F, -Br, -Cl, -I or-CN) is substituted.
As host materials of the first and second electron transport layers (310, 410) that can be used in other embodiments, materials having low HOMO energy levels can be used. For example, the HOMO levels of the host materials of the first and second electron transport layers (310, 410) may be smaller than the HOMO level of the organic material layer of the light emitting unit (210) adjacent to the second electron transport layer (410). Although not particularly limited, the lower the HOMO levels of the host materials of the first and second electron transport layers (310, 410) compared to the HOMO levels of the organic material layers of the light emitting unit (210) adjacent to the second electron transport layer (410), the better effect can be shown.
As a specific example, a compound having a functional group selected from the group consisting of an imidazolyl group, an oxazolyl group, a thiazolyl group, a quinolyl group, and a phenanthrolinyl group may be used as a host material. As other examples, an organometallic complex compound of a type containing at least one of an alkali metal ion, an alkaline earth metal ion and a rare earth metal ion may be used as a host material, and as a ligand of the organometallic complex, a quinoline may be usedExamples of the organic solvent include, but are not limited to, a hydrocarbon alcohol, a benzoquinolinol, an acridinol, a phenanthridinol, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxydiaryloxadiazole, a hydroxydiarylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxybenzotriazole, a hydroxyfluoroborane, a bipyridine, a phenanthroline, a phthalocyanine, a porphyrin, a cyclopentadiene, a β -diketone, an azomethine, and the like. Specifically, Alq may be used3BAlq, etc. as organometallic complexes.
As a specific example, a compound having the following structural formula can be used as a host material.
Wherein,
ar is an aryl group, and for example, may be a substituent represented by the following formula,
and examples of the above X include the following formulae:
herein, Z is a moiety attached to the core, and
in the above formula, each of R1 to R5 may include an alkyl group, for example, methyl, ethyl, propyl, and butyl, and may be a group including an electron-withdrawing atom (for example, -F, -Br, -Cl, -I, or-CN).
R1 'to R5' are each a group containing an electron-withdrawing atom (e.g., -F, -Br, -Cl, -I, or-CN).
In addition, a compound having the following chemical formula may be used as the first electron transport layer material.
In the above formula, R and R' are each C1-C20Alkyl or C6-C20Aryl, and
y is an arylene group, such as phenylene or naphthylene.
Specifically, the compounds having the above chemical formula include compounds having the following chemical formula:
specific examples of the second electron transport layer material include the following compounds, but are not limited thereto.
The first electron transport layer may be formed of the same material as that of the second electron transport layer described above, and in this case, may further include a compound having the following chemical formula:
in the above formula, X is represented by the following formula:
z is a moiety attached to the core structure, an
R1 to R5 each can include an alkyl group, e.g., methyl, ethyl, propyl, and butyl, and can be a group that includes an electron withdrawing atom (e.g., -F, -Br, -Cl, -I, or-CN).
In fig.1, as shown, only two light emitting cells (210, 220) are provided between the first electrode (110) and the second electrode (120), however, according to other embodiments of the present invention, more than three light emitting cells may be provided between the first electrode (110) and the second electrode (120). A case where three or more light emitting units are provided is illustrated in fig. 6.
Fig.6 illustrates a layer structure of an organic light emitting device including n light emitting units. After the light emitting unit (210), a second electron transport layer (310), a first electron transport layer (410), a charge generation layer (510), a light emitting unit (220), a second electron transport layer (320), a first electron transport layer (420), and a charge generation layer (520) are stacked on the first electrode (110), and further, the light emitting unit, the second electron transport layer, the first electron transport layer, and the charge generation layer may be sequentially repeatedly stacked. Then, after the n-1 th light emitting unit, a second electron transport layer, a first electron transport layer, and a charge generation layer are stacked, and the n-th light emitting unit is stacked with a second electrode (120). In fig.6, a structure in which the remaining layers are stacked on the first electrode is shown by illustration, but conversely, a structure in which the remaining layers are stacked on the second electrode is also included.
In an organic light emitting device according to other embodiments of the present invention, an additional electron transport layer is provided between the second electrode (120) and the light emitting unit (220) adjacent to the second electrode (120), the additional electron transport layer including a first electron transport layer (320) doped with an n-type dopant and a second electron transport layer (420) doped with a metal salt, a metal oxide, or an organic metal salt. An example of such provision of an additional electron transport layer is shown in figure 7. The description of the first electron transport layer (310) and the second electron transport layer (410) above may be applied to the first electron transport layer (320) and the second electron transport layer (420).
In an organic light emitting device according to another embodiment of the present invention, an additional electron transport layer is provided between the second electrode (120) and the light emitting unit (220) adjacent to the second electrode (120), and the additional electron transport layer includes a first electron transport layer (320) doped with an n-type dopant and a second electron transport layer (420) doped with a metal salt, a metal oxide, or an organic metal salt. Furthermore, a further charge generation layer (520) is provided between the second electrode and the further electron transport layer. An example of such provision of an additional electron transport layer and an additional charge generation layer is shown in fig. 8. The description of the charge generation layer (510) as described above may be applied to the charge generation layer (520).
In an organic light emitting device according to still another embodiment of the present invention, an additional charge generation layer (520) is provided between the second electrode and the light emitting cell (220) adjacent to (120) the second electrode (120). An example of such provision of an additional charge generation layer is shown in fig. 9. The description of the charge generation layer (510) as described above can be applied to the charge generation layer (520). According to the device of fig.9, the light emitting layer or the electron transport layer may be n-type doped.
With the structures of fig.7 to 9, materials having a greater variety of work functions can be used as the second electrode (120) material.
The organic light emitting device of the embodiment described in the present invention may be formed of a top emission type, a bottom emission type, or a dual emission type. In this case, a transparent electrode for passing light can be formed depending on the direction of light emission. The transparency is not limited to the light transmittance as long as light can pass through, but for example, may be 70% or more light transmittance. The transparent electrode may be prepared using a transparent material, or may be formed of a non-transparent material that is so thin as to be transparent.
As the material of the first electrode and the second electrode, a material having a fermi level of 2 to 6eV, particularly 2 to 4eV, can be used. The electrode material may comprise a material selected from the group consisting of metals, metal oxides and electrical conductivityA polymer. Specifically, the electrode material includes carbon, cesium, potassium, lithium, calcium, sodium, magnesium, zirconium, indium, aluminum, silver, tantalum, vanadium, chromium, copper, zinc, iron, tungsten, molybdenum, nickel, gold, other metals, and alloys thereof; zinc oxide, indium oxide, tin oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and metal oxides similar thereto; and mixtures of oxides with metals, e.g. ZnO, Al and SnO2Sb. In other words, the electrode may be formed as a metal electrode, and may also be formed as a transparent electrode made of a transparent material (e.g., metal oxide). The first electrode material and the second electrode material may be the same or may be different from each other if desired.
An organic light emitting device according to an embodiment of the present invention may have the following structure: a first electrode connected to the substrate serves as an anode, and a second electrode facing the first electrode serves as an anode. The organic light emitting device according to other embodiments of the present invention may have the following structure: the second electrode connected to the substrate serves as a cathode, and the first electrode facing the second electrode serves as an anode.
An organic light emitting device according to an embodiment of the present invention may be a device including a light scattering structure.
In one embodiment of the present invention, the organic light emitting device may further include a substrate on a surface opposite to a surface of the light emitting unit on which the first electrode is provided, and may further include a light scattering layer between the substrate and the first electrode, or on a surface opposite to the surface on which the first electrode is provided.
In one embodiment of the present invention, an internal light scattering layer may be further included between the first electrode and the substrate, wherein the substrate is provided on a surface opposite to a surface of the light emitting unit where the first electrode is provided. In another embodiment, an external light scattering layer may be additionally included in the substrate on a surface opposite to a surface on which the first electrode is provided.
In the present invention, the inner light scattering layer or the outer light scattering layer is not particularly limited as long as it has a structure that can improve the light scattering efficiency of the device by inducing light scattering. In one embodiment, the light scattering layer may have a structure in which scattering particles are distributed in a binder. In another embodiment, the light scattering layer may use a thin film that is not flat.
In addition, the light scattering layer may be directly formed on the substrate by using a method such as spin coating (spin coating), bar coating (bar coating), and slit coating (slit coating), or may be formed by using a method of preparing the light scattering layer in a thin film type and bonding the light scattering layer.
In an embodiment of the present invention, the organic light emitting device is a flexible organic light emitting device. In this case, the substrate comprises a flexible material. As examples thereof, a bendable film type glass, plastic, or film type substrate may be used.
The material of the plastic substrate is not particularly limited, however, films in the form of a single layer or a plurality of layers, such as PET, PEN, and PI, may be generally used.
In one embodiment of the present invention, a display comprising an organic light emitting device is provided.
In one embodiment of the present invention, a lighting device comprising an organic light emitting device is provided.
Hereinafter, various embodiments and features of the present invention will be described in more detail with reference to examples and comparative examples. However, it should be understood that the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
Example 1
Formed on a glass substrate by sputteringUsing thermal vacuum deposition (thermal vacuum deposition), on which the HAT of the above chemical formula 2-1 is formed as a film havingA film of thickness, then, formed using NPB to have A layer of thickness. Is formed thereonA fluorescent blue light emitting layer of thickness and formed by doping 50 wt% of LiF into the following material 1A second electron transport layer of thickness. By doping 10% by weight of Ca into the following material 1, formed thereon withA first electron transport layer of thickness.
Material 1
Then useHAT layer ofForming a charge generation layer and forming a thicknessThe phosphorescent green and red light emitting layers. Next, the following material 2 was used to form a thicknessAnd finally, forming an electron transport layer having a thickness ofLIF and a thickness ofTo produce a white organic light emitting device having a layer structure.
Material 2
Example 2
A device was fabricated in the same manner as in example 1, except that a second electron transport layer was formed by doping 50 wt% of Liq, an organometallic salt, to the above material 1.
Comparative example 1
A device was manufactured in the same method as in example 1, except that the material 1 not doped with the metal salt or the organic metal salt was used to formA second electron transport layer of thickness.
At 3mA/cm2The voltage and efficiency formed by examples 1 and 2 and comparative example 1 were area-measured, and the results of comparison are shown in table 1 below.
[ Table 1]
| Example 1 | Example 2 | Comparative example 1 | |
| Voltage (V) | 6.3 | 6.3 | 7.3 |
| Current efficiency (cd/A) | 48 | 50 | 45 |
Example 3
A device was manufactured in the same manner as in example 1, except that the above-described material 2 was used instead of the above-described material 1 when the second electron transit layer and the first electron transit layer were formed.
Comparative example 2
A device was fabricated in the same manner as in example 3, except that the material 2 not doped with a metal salt or an organic metal salt was used to form a thicknessThe second electron transport layer.
Comparative example 3
A device was manufactured in the same manner as in example 3, except that the first electron transporting layer was not formed and was formed to a thicknessThe second electron transport layer of (1).
Comparative example 4
A device was fabricated in the same manner as in example 3, except that the second electron transport layer was not formed and was formed to a thicknessThe first electron transport layer of (1).
At 3mA/cm2The area measurement of the formed voltage and efficiency of example 3 and comparative examples 2 to 4, and the comparative results thereof are shown in table 2 below.
[ Table 2]
| Example 3 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| Voltage (V) | 5.6 | 6.3 | 15.0 | 6.5 |
| Current efficiency (cd/A) | 55 | 52 | 43 | 40 |
Example 4
Formed on a glass substrate by sputteringOn which HAT of the above chemical formula 2-1 is formed as a film having the same structure as that of the ITO of (1) as an anode using thermal vacuum depositionFilm thickness, then, formation using NPBA layer of thickness. Is formed thereonA fluorescent blue light emitting layer of thickness and formed by doping 50 wt% of LiF into the above material 2A second electron transport layer of thickness. By doping 10% by weight of Ca into the above-mentioned material 2, a film having Ca was formed thereonA first electron transport layer of thickness.
Then useHAT layer ofForming a charge generation layer and forming a thicknessThe phosphorescent green and red light emitting layers. Next, by co-depositing 50 wt% LiF into the above-mentioned material 2, a film was formedA second electron transport layer of thickness and formed thereon by doping 10 wt% of calcium into the above-mentioned material 2A first electron transport layer of thickness. Finally, a film having a thickness ofTo produce a white organic light emitting device having a layer structure.
Comparative example 5
A device was prepared in the same composition and method as in example 4, except that the second electron transport layer and the first electron transport layer were not formed on the portion adjacent to the charge generation layer, and the second electron transport layer and the first electron transport layer were formed only on the portion adjacent to the cathode.
At 3mA/cm2The voltage and efficiency formed by example 4 and comparative example 5 were area-measured, and the results of comparison are shown in table 3 below.
[ Table 3]
| Example 4 | Comparative example 5 | |
| Voltage (V) | 5.6 | 15.0 |
| Current efficiency (cd/A) | 52 | 40 |
Example 5
A device was produced in the same manner as in example 1, except that when the second electron transport layer and the first electron transport layer were formed on portions adjacent to the charge generation layer, the following material 5 was used instead of the material 1.
Material 5
Example 6
A device was produced in the same manner as in example 1 except that when the second electron transport layer and the first electron transport layer were formed on portions adjacent to the charge generation layer, the following material 7 was used instead of the material 1.
Material 7
Example 7
A device was produced in the same manner as in example 1 except that when the second electron transport layer and the first electron transport layer were formed on portions adjacent to the charge generation layer, the following material 9 was used instead of the material 1.
Material 9
Example 8
A device was produced in the same manner as in example 1, except that when the second electron transport layer and the first electron transport layer were formed on portions adjacent to the charge generation layer, the following material 11 was used instead of the material 1.
Material 11
At 3mA/cm2The area measurements of the voltage and efficiency formed by examples 5 to 8 are shown in Table 4 below.
[ Table 4]
| Example 5 | Example 6 | Example 7 | Example 8 | |
| Voltage (V) | 5.6 | 5.6 | 5.6 | 5.5 |
| Current efficiency (cd/A) | 55 | 55 | 55 | 55 |
Example 9
A device was fabricated in the same manner as in example 1, except that in a portion adjacent to the charge generation layer, 50 wt% of LiF was co-deposited into the above-mentioned material 2 to form a thicknessAnd a second electron transport layer formed by doping 10 wt% of Ca into the following material 13 to have a thicknessThe first electron transport layer of (1).
Material 13
Example 10
A device was produced in the same manner as in example 9, except that, in forming the first electron transport layer, 5 wt% of Ca was doped in a portion adjacent to the charge generation layer.
Example 11
A device was produced in the same manner as in example 9, except that, in forming the first electron transport layer, in a portion adjacent to the charge generation layer, Ca doping was performed at 2.5 wt%.
Comparative example 6
A device was produced in the same manner as in example 9, except that in a portion adjacent to the charge generation layer, only the above-described material 2 containing no metal salt or organic metal salt was used to form a thicknessAnd a second electron transport layer formed by doping 10 wt% of Ca into the above material 13 to a thicknessThe first electron transport layer of (1).
Comparative example 7
A device was fabricated in the same manner as in example 9, except that the thickness was formed by doping 10 wt% of CaThus, the second electron transport layer is formed of the same material as the material doped to the first electron transport layer.
Comparative example 8
A device was fabricated in the same manner as in example 9, except that the thickness was formed by doping 50 wt% of LiFThus, the first electron transport layer is formed of the same material as that doped to the second electron transport layer.
Comparative example 9
A device was prepared in the same manner as in example 9, except that HAT of the n-type charge generation layer adjacent to the first electron transport layer was not formed.
At 3mA/cm2The formed voltages and efficiencies of examples 9 to 11 and comparative examples 6 to 9 were area-measured, and the comparative results are shown in table 5 below.
[ Table 5]
| Voltage (V) | Current efficiency (cd/A) | |
| Example 9 | 5.6 | 55 |
| Example 10 | 5.6 | 58 |
| Example 11 | 5.5 | 60 |
| Comparative example 6 | 5.8 | 55 |
| Comparative example 7 | 6.0 | 30 |
| Comparative example 8 | 14.0 | 44 |
| Comparative example 9 | 16.0 | 42 |
Fig.10 and 11 show voltage-current and lifetime plots for the device doped with a second electron transport layer of a metal salt such as LiF (example 11) versus the device undoped second electron transport layer (comparative example 6). It can be shown that the device of the second electron transport layer doped with a metal salt or the like has a lower initial voltage, experiences a very small increase in voltage when driven, and has an increase in service life, compared to the device of the undoped second electron transport layer.
In comparative examples 7 and 8, in the device, the material doped to the second electron transport layer and the material doped to the first electron transport layer were the same, and Ca and LiF were used to dope the device, respectively.
In comparative example 7, the efficiency of the device is rapidly decreased because the Ca doping layer is adjacent to the light emitting layer, and thus this phenomenon occurs due to light emitting quenching (light emitting quenching). In addition, when both the first electron transport layer and the second electron transport layer are doped with an n-type dopant, light absorption may be increased. When the second electron transport layer adjacent to the light emitting layer is doped with a metal, light emitting efficiency may be reduced.
In comparative example 8, since LiF is doped to the first electron transport layer to have an insulating property, the driving voltage is significantly increased, and the n-type charge generation layer does not react with HAT, and thus, it is not easy to inject electrons from the HAT layer to the first electron transport layer.
In comparative example 9, no emission of blue light from the first light emitting unit was observed, and only emission of yellow light from the second light emitting unit was observed, which means that the series structure did not function effectively because the HAT, n-type charge generation layer was not generated.
Claims (34)
1. An organic light emitting device comprising:
a first electrode;
a second electrode; and
two or more light emitting cells provided between the first electrode and the second electrode,
wherein, in the light emitting units, the charge generation layer is provided between two light emitting units adjacent to each other; the electron transport layer is provided between the charge generation layer and the light emitting cells disposed adjacent to the first electrodes of two adjacent light emitting cells, and includes a first electron transport layer doped with an n-type dopant and a second electron transport layer doped with a metal salt, a metal oxide or an organic metal salt.
2. An organic light-emitting device according to claim 1 wherein the first electron transport layer is provided between the second electron transport layer and the charge generation layer.
3. The organic light emitting device according to claim 1, wherein an additional electron transport layer is provided between the second electrode and the light emitting unit adjacent to the second electrode, and the additional electron transport layer comprises a first electron transport layer and a second electron transport layer, wherein the first electron transport layer is doped with an n-type dopant and the second electron transport layer is doped with a metal salt, a metal oxide, or an organic metal salt.
4. An organic light-emitting device according to claim 3 wherein a further charge-generating layer is provided between the second electrode and the further electron-transporting layer.
5. An organic light-emitting device according to claim 1 wherein a further charge-generating layer is provided between the second electrode and the light-emitting unit adjacent to the second electrode.
6. The organic light emitting device of claim 1, wherein the charge generation layer comprises an n-type organic material layer and a p-type organic material layer.
7. The organic light emitting device according to claim 6, wherein a LUMO energy level of the n-type organic material layer of the charge generation layer is equal to or greater than a HOMO energy level of the p-type organic material layer of the charge generation layer.
8. The organic light-emitting device according to claim 6, wherein a difference between a HOMO level of the p-type organic material layer of the charge generation layer and a LUMO level of the n-type organic material layer of the charge generation layer is 2eV or less.
9. The organic light-emitting device according to claim 6, wherein the LUMO level of the n-type organic material layer of the charge generation layer is 5eV to 7 eV.
10. The organic light-emitting device according to claim 6, wherein the HOMO level of the p-type organic material layer of the charge generation layer is 5eV or more.
11. The organic light emitting device according to claim 6, wherein the n-type organic material layer of the charge generation layer comprises a compound of the following chemical formula 2:
[ chemical formula 2]
In chemical formula 2, A1To A6Each is hydrogen, halogen atom, cyano (-CN), nitro (-NO)2) Sulfonyl (-SO)2R), sulfoxide group (-SOR), sulfonamide group (-SO)2NR), sulfate (-SO)3R), trifluoromethyl (-CF)3) An ester group (-COOR), an amide group (-CONHR or-CONRR'), a substituted or unsubstituted straight or branched C1-C12Alkoxy, substituted or unsubstituted straight or branched C1-C12Alkyl, substituted or unsubstituted straight or branched C2-C12Alkenyl, substituted or unsubstituted aromatic or non-aromatic heterocycle, substituted or unsubstituted aryl, substituted or unsubstituted mono-or diarylamine, substituted or unsubstituted aralkylamine, and
r and R' are each substituted or unsubstituted C1-C60An alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted 5 to 7 membered heterocyclic ring.
12. The organic light emitting device according to claim 11, wherein the compound of the above chemical formula 2 is represented by any one of the following chemical formulae 2-1 to 2-6:
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2 to 3]
[ chemical formulas 2-4]
[ chemical formulas 2 to 5]
[ chemical formulas 2 to 6]
13. An organic light-emitting device according to claim 1 wherein the n-type dopant of the first electron-transporting layer comprises one or more species selected from the following types: alkali metals, alkaline earth metals, rare earth metals, and metal compounds.
14. The organic light emitting device according to claim 1, wherein the n-type dopant of the first electron transport layer comprises one or more metals selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Be, Mg, Ca, Sr, Ba, Ra, La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y, Mn and metal compounds including one or more metals selected from the above metals.
15. The organic light emitting device of claim 1, wherein the n-type dopant content in the first electron transport layer is from 1 to 50 wt% based on the total weight of the first electron transport layer.
16. The organic light emitting device of claim 1, wherein the first electron transport layer has a thickness ranging from 50 angstroms to 100 angstroms.
17. An organic light-emitting device according to claim 1 wherein the second electron-transporting layer is doped with a halide or oxide of an alkali or alkaline earth metal or with an organometallic complex.
18. An organic light-emitting device according to claim 1 wherein the second electron-transporting layer is doped with one or more compounds selected from the group consisting of: LiF, NaF, KF, RbF, CsF, MgF2、CaF2、SrF2、BaF2、LiCl、NaCl、KCl、RbCl、CsCl、MgCl2、CaCl2、SrCl2、BaCl2、LiO2、NaO2、BrO2、Cs2O, MgO, CaO, Liq, Naq and Kq.
19. The organic light emitting device according to claim 1, wherein the content of the metal salt, the metal oxide or the organic metal salt in the second electron transport layer ranges from 10 to 50% by weight based on the total weight of the second electron transport layer.
20. An organic light-emitting device according to claim 1 wherein the second electron-transporting layer has a thickness in the range of 50 angstroms to 500 angstroms.
21. The organic light-emitting device according to claim 1, wherein the light-emitting unit comprises one or more light-emitting layers.
22. The organic light-emitting device according to claim 21, wherein the light-emitting unit further comprises one or more layers of a hole-transporting layer, a hole-injecting layer, a layer for transporting and injecting holes, a buffer layer, an electron-blocking layer, an electron-transporting layer, an electron-injecting layer, a layer for transporting or injecting electrons, and a hole-blocking layer.
23. An organic light-emitting device according to any of claims 1 to 22 wherein the first and second electron transport layers each independently comprise: an electron transport layer material having an n-type substituent in the anthracene core, an electron transport material having an n-type substituent in the dianthracene core, or an organometallic complex.
24. An organic light-emitting device according to any of claims 1 to 22 wherein the first and second electron transport layers each independently comprise one or more types of compounds having a functional group selected from: imidazolyl, oxazolyl, thiazolyl, quinolinyl and phenanthrolinyl; and an organometallic complex compound containing at least one type of alkaline earth metal ion and rare earth metal ion.
25. The organic light emitting device of claim 23, wherein the ligand of the organometallic complex is selected from the group consisting of quinolinols, benzoquinolinols, acridinols, phenanthridinols, hydroxyphenyloxazoles, hydroxyphenylthiazoles, hydroxydiaryl oxadiazoles, hydroxydiaryl thiadiazoles, hydroxyphenylpyridines, hydroxyphenylbenzimidazoles, hydroxybenzotriazoles, hydroxyfluoroboranes, bipyridines, phenanthrolines, phthalocyanines, porphyrins, cyclopentadienes, β -diketones, and azomethines.
26. An organic light-emitting device according to any of claims 1 to 22 wherein the first and second electron-transporting layers each independently comprise one or more compounds selected from the group having the following structural formula:
in the above-mentioned formula, the compound of formula,
ar is aryl,
X is selected from the following structural formulas,
z is a moiety attached to the core,
r1 to R5 are each a group containing an alkyl group or an electron-withdrawing atom, and
r1 'to R5' are each a group containing an electron-withdrawing atom.
27. An organic light-emitting device according to any of claims 1 to 22 wherein the first electron-transporting layers each independently comprise one or more compounds selected from compounds having the following structural formula:
in the above-mentioned formula, the compound of formula,
r and R' are each C1-C20Alkyl or C6-C20Aryl, and
y is an arylene group.
28. The organic light-emitting device according to any one of claims 1 to 22, wherein the first electron transport layers each independently comprise one or more types of compounds selected from the group consisting of compounds having a structural formula of the following group 1, and one or more types of compounds selected from the group consisting of compounds having a structural formula of the following group 2:
[ group 1]
[ group 2]
In the above formula, X represents the following formula,
z is a moiety attached to the core structure, an
R1 to R5 are each a group containing an alkyl group or an electron-withdrawing atom.
29. An organic light-emitting device according to any of claims 1 to 22 wherein the second electron-transporting layers each independently comprise one or more types of compounds selected from compounds having the following structural formula:
30. the organic light emitting device according to claim 29, wherein the second electron transport layer comprises an organometallic salt of the following chemical formula 3,
[ chemical formula 3]
X＝Li，Na，K。
31. An organic light-emitting device according to any one of claims 1 to 22 further comprising:
a substrate on a surface opposite to a surface of the light emitting unit on which the first electrode is provided; and
a light scattering layer located between the substrate and the first electrode or on a surface opposite to a surface on which the first electrode is provided.
32. An organic light-emitting device according to any of claims 1 to 22 wherein the organic light-emitting device is a flexible organic light-emitting device.
33. A display comprising the organic light emitting device of any one of claims 1 to 22.
34. A lighting device comprising the organic light-emitting device according to any one of claims 1 to 22.
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| PCT/KR2013/004787 WO2013180503A1 (en) | 2012-05-31 | 2013-05-31 | Organic light emitting diode |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2752907A1 (en) | 2014-07-09 |
| EP2752907B1 (en) | 2019-07-17 |
| US20150144897A1 (en) | 2015-05-28 |
| WO2013180503A1 (en) | 2013-12-05 |
| TW201421760A (en) | 2014-06-01 |
| KR20130135161A (en) | 2013-12-10 |
| TWI622196B (en) | 2018-04-21 |
| JP5973661B2 (en) | 2016-08-23 |
| CN104272488B (en) | 2017-09-08 |
| EP2752907A4 (en) | 2015-07-29 |
| KR101653212B1 (en) | 2016-09-01 |
| US9831457B2 (en) | 2017-11-28 |
| JP2015518287A (en) | 2015-06-25 |
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